Polyamide compositions for sealants and high solids paints

ABSTRACT

A polyamide composition for use in sealants, adhesives and high solids coatings.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority benefit from U.S. Provisional PatentApplication 62/199,499 filed Jul. 31, 2015 and U.S. Provisional PatentApplication 62/214,487 filed Sep. 4, 2015, each of which is incorporatedby reference herein in its entirety.

FIELD OF THE INVENTION

The present invention relates a polyamide composition and the use ofsuch a polyamide composition as a rheological additive in sealants,adhesives, and high solids coating systems.

BACKGROUND OF THE INVENTION

Hydrogenated castor oil is a good organic thixotrope or “rheologicaladditive” (RA) because it provides excellent performance when theadditive is dispersed and activated in a specific manner. Therheological additive provides anti-settling effects, and controls flowand leveling as well as the degree of sagging in paints and coatings.The glyceride moiety in castor wax can be replaced by amine functionalmaterials to yield wax like amides of 12-hydroxy stearic acid. Theseamides are also quite effective as rheological control agents, and theycomplement hydrogenated castor oil to yield an effective castor waxportfolio of materials for the paint formulator to choose from. Thecastor derived 12-hydroxystearic acid moiety is an effective rheologicalcomponent because it can self-assemble into spatially preferredstructures, some of which extend throughout the formulation andeffectively trap solvent and/or resin and thereby control the materialflow.

Prior art polyamide based rheological additives have specific processingtemperature requirements that are related to the solvency effectspresent in a paint system or a sealant system. Therefore, the mostappropriate choice of polyamide rheological additives for any givensystem depends on solvent type(s), processing temperature control andthe manufacturing equipment. An optimal combination of these parametersallows for the most effective level of colloidal dispersion and yields arheologically active network.

However, problems can arise when the paint processing temperature is toohigh for the additive—the polyamide rheological additive can dissolvecompletely at these elevated temperatures and later on, as the systemcools down, the additive can precipitate and form semi-crystallineparticulate matter, which is sometimes also referred to as “seeds”. Asimilar seeding situation can occur when the solvent/temperaturecombination is too strong. The immediate seeding effect typically can beobserved relatively quickly. A more complex seeding situation may occurwhen the additive is not processed enough or not enough solvent ispresent. In these cases potentially, not all powdered wax material hasbeen converted into the desirable rheologically active form and unusedmaterial remains behind, often unnoticed at the point of paintmanufacture. Over time upon storage, this unused additive material cantransform under the influence of solvent, ambient temperature and time,to yield particles that lead to loss of fineness of grind and reducedgloss of the paint system, or activate overtime to become rheologicallyactive.

For sealant, adhesive and coating compositions, long term storage aboveroom temperature can lead to activation of the unactive polyamideadditive which results in an undesirable increase in viscosity of suchcomposition.

The present invention provides for rheological additives that activateeasily and can be used in high solids paint systems or MS polymersealants.

SUMMARY OF THE INVENTION

In one embodiment, the present disclosure provides for a polyamidecomposition consisting essentially of or consisting of a polyamidehaving groups derived from: a diamine selected from the group consistingof ethylene diamine and hexamethylene diamine; a straight chainmonocarboxylic acid having 1 to 5 carbon atoms; a fatty acidindependently selected from the group consisting of: 12-hydroxystearicacid, lesquerolic acid and combinations thereof; wherein the diamine,the straight chain monocarboxylic acid and fatty acid have a molarequivalent ratio ranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5to 1:1:1; and a median particle size ranging from 1 μm to 10 μm. In somesuch embodiments, the straight chain monocarboxylic acid isindependently selected from the group consisting of: acetic acid,propionic acid, butyric acid, valeric acid, and combinations thereof.

In certain embodiments of the polyamide, the diamine is ethylenediamine, the straight chain monocarboxylic acid is acetic acid and thefatty acid is 12-hydroxystearic acid wherein ethylene diamine, aceticacid and 12-hydroxystearic acid have a molar equivalent ratio rangingfrom 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1.

In certain embodiments of the polyamide, the diamine is ethylenediamine, the straight chain monocarboxylic acid is propionic acid andthe fatty acid is 12-hydroxystearic acid, wherein ethylene diamine,proprionic acid and 12-hydroxystearic acid have a molar equivalent ratioranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1.

In each of the foregoing embodiments of polyamides, the median particlesize may range from 3 μm to 7 μm.

In another embodiment, the present disclosure provides for a curablesealant or adhesive composition comprising a resin; an optional catalystor optional curing agent or optional solvent, a polyamide compositionhaving a median particle size ranging from 1 μm to 10 μm; or 3 μm to 7μm; wherein the polyamide composition has an activation temperatureranging between 25° C. and 50° C.; or 30° C. and 45° C. in curablesealant or adhesive composition. In another embodiment, the presentdisclosure provides for a method of making a curable sealant or adhesivecomposition. In some embodiments of the curable sealant or adhesivecomposition and its method of making, the resin is a silyl-terminatedpolymer independently selected from the group consisting of: silylatedpolyurethane, silylated polyether polyol, silylated polyester, silylatedpolybutadiene, and combinations thereof. Such polymers are known in theart as MS-Polymers and SPUR. In such embodiment, the curable sealant oradhesive composition is moisture curable.

In yet another embodiment, the present disclosure provides for a highsolids coating composition comprising: a first pack and a second pack;wherein the first pack comprises: (a) at least one resin (b) a polyamidecomposition; and (c) a diluent; and the second pack comprises: at leastone cross linking agent; wherein the high solids composition has asolids content of at least 70 wt. %, and wherein the polyamide isactivated upon mixing the ingredients of pack one between 25° C. and 50°C.

DETAILED DESCRIPTION OF THE EMBODIMENTS

The present disclosure provides for a polyamide composition and its useas a rheology modifier in one and two component sealant and adhesivecompositions, such as silylated polymer sealant compositions, and paintcompositions including high solids and 100% solids paint. A skilledperson would understand that a polyamide has two or more amide groups.

In current manufacturing processing of sealant, adhesive and coatingcompositions, the processing conditions are adjusted (temperature, shearrate, time) to accommodate the characteristics of the commerciallyavailable polyamide rheological additives. Various embodiments ofrheological additives are described herein to allow for manufacturingprocesses that can yield cost savings by reducing production time andenergy costs (such as no additional heat requirement).

Furthermore, paint manufacturers are moving to higher solids paintformulations, to avoid volatile organic diluents. Therefore, there isless organic solvent to facilitate incorporation and/or activation ofrheological additives in such systems. The present disclosure providesfor various embodiments of polyamides which avoid the necessity ofpre-activation in organic solvents.

In one embodiment, the present disclosure provides for a polyamidecomposition consisting essentially of a polyamide having groups derivedfrom: a diamine independently selected from the group consisting ofethylene diamine and hexamethylene diamine; a straight chainmonocarboxylic acid having 1 to 5 carbon atoms; a fatty acidindependently selected from the group consisting of: 12-hydroxystearicacid, lesquerolic acid and combinations thereof; wherein the diamine,the straight chain monocarboxylic acid and fatty acid have a molarequivalent ratio ranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5to 1:1:1; and a median particle size ranging from 1 μm to 10 μm. In someof the foregoing embodiments, the straight chain monocarboxylic acid isindependently selected from the group consisting of: acetic acid,propionic acid, butyric acid, valeric acid, and combinations thereof. Incertain of the foregoing embodiments, the straight chain monocarboxylicacid is independently selected from the group consisting of: aceticacid, propionic acid, and combinations thereof.

A skilled person would understand that 12-hydroxystearic acid is derivedfrom castor oil, and typically is not 100% hydroxystearic acid.

In certain embodiments, the composition consists essentially of apolyamide wherein the diamine is ethylene diamine, the straight chainmonocarboxylic acid is acetic acid and the fatty acid is12-hydroxystearic acid wherein ethylene diamine, acetic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1.

In certain embodiments, the composition consists essentially of apolyamide wherein the diamine is ethylene diamine, the straight chainmonocarboxylic acid is propionic acid and the fatty acid is12-hydroxystearic acid wherein ethylene diamine, propionic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1.

In some of the foregoing embodiments, the median particle size, of thepolyamide, may range from 3 μm to 7 μm.

For the purposes of this application, “consisting essentially of” shallmean materials which do not materially affect the basic and novelcharacteristic of the polyamide. Materials which may materially affectthe basic and novel characteristic of the polyamide include, but notlimited to: polyamides based on 12-hydroxystearic acid, polyamines andmonocarboxylic acids with more than 7 carbon atoms; and mixtures ofpolyamides based on (i) 12-hydroxystearic acid, polyamines andmonocarboxylic acids with more than 7 carbon atoms and (ii)12-hydroxystearic acid, polyamines and monocarboxylic acids with 3-4carbon atoms. Materials which also may materially affect the basic andnovel characteristic of the polyamide include those that increase theactivation temperature of a high solids paint composition or sealantcomposition containing the polyamide.

For the purposes of this application, “activation” shall mean atransformation where the polyamide is physically transformed into a formwhich imparts thixotropic behavior. Temperature or other forms of energyinput can facilitate this activation. In one embodiment, the physicaltransformation is from powder like material to material with fiber likemorphology.

In one embodiment, the present disclosure provides for a polyamidecomposition consisting of a polyamide having groups derived from: adiamine selected from the group consisting of ethylene diamine andhexamethylene diamine; a straight chain monocarboxylic acid having 1 to5 carbon atoms; a fatty acid independently selected from the groupconsisting of: 12-hydroxystearic acid, lesquerolic acid and combinationsthereof; wherein the diamine, the straight chain monocarboxylic acid andfatty acid have a molar equivalent ratio ranging from 1:1.75:0.25 to1:0.75:1.25; or 1:1.5:0.5 to 1:1:1; and a median particle size rangingfrom 1 μm to 10 μm. In certain of the foregoing embodiments, thestraight chain monocarboxylic acid is independently selected from thegroup consisting of: acetic acid, propionic acid, butyric acid, valericacid, and combinations thereof. In certain of the foregoing embodiments,the straight chain monocarboxylic acid is independently selected fromthe group consisting of: acetic acid, propionic acid, and combinationsthereof.

In some embodiments, the composition consists of a polyamide wherein thediamine is ethylene diamine, the straight chain monocarboxylic acid isacetic acid and the fatty acid is 12-hydroxystearic acid whereinethylene diamine, acetic acid and 12-hydroxystearic acid have a molarequivalent ratio ranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5to 1:1:1.

In some embodiments, the composition consists of a polyamide wherein thediamine is ethylene diamine, the straight chain monocarboxylic acid ispropionic acid and the fatty acid is 12-hydroxystearic acid whereinethylene diamine, propionic acid and 12-hydroxystearic acid have a molarequivalent ratio ranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5to 1:1:1.

In some of the foregoing embodiments, the median particle size, of thepolyamide, may range from 3 μm to 7 μm.

In another embodiment, the present disclosure provides for a curablesealant or adhesive composition comprising a resin; an optional catalystor optional curing agent or optional solvent, a polyamide compositionhaving a median particle size ranging from 1 μm to 10 μm; or 3 μm to 7μm; wherein the polyamide composition has an activation temperatureranging between 25° C. and 50° C.; or 30° C. and 45° C. in curablesealant or adhesive composition. In another embodiment, the presentdisclosure provides for a method of making a curable sealant or adhesivecomposition. The method comprises the steps of: adding a polyamidecomposition to a resin; blending the mixture of the polyamide and theresin at a temperature ranging between 25° C. and 50° C. In suchembodiments, the amount of polyamide composition may range from 0.5 wt.% to 3 wt. %. In some other such embodiments, the amount of catalyst mayrange from 0.1 wt. % to 1.0 wt. %.

In another embodiment, the present disclosure provides for a curablesealant or adhesive composition, the composition is contained in a oneor two pack system. For the two pack system, the resin and polyamideaccording to the various embodiments described herein, and othercomponents, described herein below, are contained in one pack; and acatalyst or curing agent, and optional components, are contained in thesecond pack. For the one pack system, the resin and polyamide accordingto the various embodiments described herein, catalyst and/or curingagent, optional pigment, filler and plasticizer, and other componentsdescribed herein below, are contained in one pack. The variousembodiments of one pack curable sealant or adhesive composition,described herein, may be substantially water free. For the purposes ofthis application, substantially water free may mean water content thatcannot be measured by standard methods such as Karl Fischer.

In some embodiments of a one part curable sealant or adhesivecomposition and its method of making, the resin is selected fromsilicone, polyurethane systems and the catalyst or curing agent areincluded in the composition. In some embodiments of a one part curablesealant or adhesive composition and its method of making, the resin isselected from acrylic and butyl rubber solvent based resins without acatalyst or curing agent. In some embodiments of a two part curablesealant or adhesive composition and its method of making, the resin isselected from epoxy resin, epoxy-penetrating solvent-based resin,silicone resin, and polyurethane resin.

In some embodiments of the curable sealant or adhesive composition andits method of making, the resin is a silyl-terminated polymerindependently selected from the group consisting of: silylatedpolyurethane, silylated polyether polyol, silylated polyester, silylatedpolybutadiene, and combinations thereof. Such polymers are known in theart as MS-Polymers and SPUR. In such embodiment, the curable sealant oradhesive composition is moisture curable.

In some such embodiments of the curable sealant or adhesive composition,either one pack or two pack, and its method of making, the polyamideconsists essentially of a polyamide having groups derived from: adiamine selected from the group consisting of ethylene diamine andhexamethylene diamine; a straight chain monocarboxylic acid having 1 to6 carbon atoms; a fatty acid independently selected from the groupconsisting of: 12-hydroxystearic acid, lesquerolic acid and combinationsthereof; wherein the diamine, the straight chain monocarboxylic acid andfatty acid have a molar equivalent ratio ranging from 1:1.75:0.25 to1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. In some such embodiments of thepolyamide of the curable sealant or adhesive composition, the straightchain monocarboxylic acid is independently selected from the groupconsisting of: propionic acid, butyric acid, valeric acid, hexanoic acidand combinations thereof. In certain of the embodiments of the polyamideof the curable sealant or adhesive composition, the straight chainmonocarboxylic acid is independently selected from the group consistingof: acetic acid, propionic acid, and combinations thereof.

In some embodiments of the curable sealant or adhesive composition, thepolyamide consists essentially of groups wherein, the diamine isethylene diamine, the straight chain monocarboxylic acid is acetic acidand the fatty acid is 12-hydroxystearic acid wherein ethylene diamine,acetic acid and 12-hydroxystearic acid have a molar equivalent ratioranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Suchpolyamide composition may have a median particle size ranging from 1 μmto 10 μm; or 3 μm to 7 μm and the polyamide composition may have anactivation temperature ranging between 25° C. and 50° C.; or 30° C. and45° C. when combined with resin and optional solvent, pigment, fillerand plasticizer. In some instances, such curable sealant or adhesivecompositions includes resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions includes resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In some embodiments of the curable sealant or adhesive composition thepolyamide consists essentially of groups wherein, the diamine isethylene diamine, the straight chain monocarboxylic acid is propionicacid and the fatty acid is 12-hydroxystearic acid wherein ethylenediamine, propionic acid and 12-hydroxystearic acid have a molarequivalent ratio ranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5to 1:1:1. Such polyamide composition may have a median particle sizeranging from 1 μm to 10 μm; or 3 μm to 7 μm and the polyamidecomposition may have an activation temperature ranging between 25° C.and 50° C.; or 30° C. and 45° C. when combined with resin and optionalsolvent, pigment, filler and plasticizer. In some instances, suchcurable sealant or adhesive compositions include resins independentlyselected from epoxy, epoxy-penetrating solvent-based resin, polyurethaneresin and combinations thereof. In some other instances, such curablesealant or adhesive compositions include resins independently selectedfrom silylated polyurethane, silylated polyether polyol, silylatedpolyester, silylated polybutadiene and combinations thereof.

In other embodiments of the curable sealant or adhesive composition thepolyamide consists essentially of groups wherein the diamine is ethylenediamine, the straight chain monocarboxylic acid is butyric acid and thefatty acid is 12-hydroxystearic acid wherein ethylene diamine, butyricacid and 12-hydroxystearic acid have a molar equivalent ratio rangingfrom 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Such polyamidecomposition may have a median particle size ranging from 1 μm to 10 μm;or 3 μm to 7 μm and the polyamide composition may have an activationtemperature ranging between 25° C. and 50° C.; or 30° C. and 45° C. whencombined with resin and optional solvent, pigment, filler andplasticizer. In some instances, such curable sealant or adhesivecompositions include resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions include resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In some embodiments of the curable sealant or adhesive composition thepolyamide consists essentially of groups wherein the diamine is ethylenediamine, the straight chain monocarboxylic acid is hexanoic acid and thefatty acid is 12-hydroxystearic acid wherein ethylene diamine, hexanoicacid and 12-hydroxystearic acid have a molar equivalent ratio rangingfrom 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Such polyamidecomposition may have a median particle size ranging from 1 μm to 10 μm;or 3 μm to 7 μm and the polyamide composition may have an activationtemperature ranging between 25° C. and 50° C.; or 30° C. and 45° C. whencombined with resin and optional solvent, pigment, filler andplasticizer. In some instances, such curable sealant or adhesivecompositions include resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions include resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In some other such embodiments of the curable sealant or adhesivecomposition and its method of making, the polyamide consists of apolyamide having groups derived from: a diamine selected from the groupconsisting of ethylene diamine and hexamethylene diamine; a straightchain monocarboxylic acid having 1 to 6 carbon atoms; a fatty acidindependently selected from the group consisting of 12-hydroxystearicacid, lesquerolic acid and combinations thereof; wherein the diamine,the straight chain monocarboxylic acid and fatty acid have a molarequivalent ratio ranging from 1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5to 1:1:1. In some such embodiments of the polyamide of the curablesealant or adhesive composition, the straight chain monocarboxylic acidis independently selected from the group consisting of propionic acid,butyric acid, valeric acid, hexanoic acid and combinations thereof. Incertain of the embodiments of the polyamide of the curable sealant oradhesive composition, the straight chain monocarboxylic acid isindependently selected from the group consisting of: acetic acid,propionic acid, and combinations thereof. Such polyamide composition mayhave a median particle size ranging from 1 μm to 10 μm; or 3 μm to 7 μmand the polyamide composition may have an activation temperature rangingbetween 25° C. and 50° C.; or 30° C. and 45° C. when combined with resinand optional solvent, pigment, filler and plasticizer. In someinstances, such curable sealant or adhesive compositions may alsoinclude resins independently selected from epoxy, epoxy-penetratingsolvent-based resin, polyurethane resin and combinations thereof. Insome other instances, such curable sealant or adhesive compositionsinclude resins independently selected from silylated polyurethane,silylated polyether polyol, silylated polyester, silylated polybutadieneand combinations thereof.

In some embodiments of the curable sealant or adhesive composition thepolyamide, consists of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is acetic acid and the fatty acidis 12-hydroxystearic acid wherein ethylene acetic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Such polyamidecomposition may have a median particle size ranging from 1 μm to 10 μm;or 3 μm to 7 μm and the polyamide composition may have an activationtemperature ranging between 25° C. and 50° C.; or 30° C. and 45° C. whencombined with resin and optional solvent, pigment, filler andplasticizer. In some instances, such curable sealant or adhesivecompositions include resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions include resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In some embodiments of the curable sealant or adhesive composition thepolyamide consists of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is propionic acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, propionic acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Such polyamidecomposition may have a median particle size ranging from 1 μm to 10 μm;or 3 μm to 7 μm and the polyamide composition may have an activationtemperature ranging between 25° C. and 50° C.; or 30° C. and 45° C. whencombined with resin and optional solvent, pigment, filler andplasticizer. In some instances, such curable sealant or adhesivecompositions include resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions include resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In other embodiments of the curable sealant or adhesive composition thepolyamide consists of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is butyric acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, butyric acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Such polyamidecomposition may have a median particle size ranging from 1 μm to 10 μm;or 3 μm to 7 μm and the polyamide composition may have an activationtemperature ranging between 25° C. and 50° C.; or 30° C. and 45° C. whencombined with resin and optional solvent, pigment, filler andplasticizer. In some instances, such curable sealant or adhesivecompositions include resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions include resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In some embodiments of the curable sealant or adhesive composition thepolyamide consists of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is hexanoic acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, hexanoic acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1. Such polyamidecomposition may have a median particle size ranging from 1 μm to 10 μm;or 3 μm to 7 μm and the polyamide composition may have an activationtemperature ranging between 25° C. and 50° C.; or 30° C. and 45° C. whencombined with resin and optional solvent, pigment, filler andplasticizer. In some instances, such curable sealant or adhesivecompositions include resins independently selected from epoxy,epoxy-penetrating solvent-based resin, polyurethane resin andcombinations thereof. In some other instances, such curable sealant oradhesive compositions include resins independently selected fromsilylated polyurethane, silylated polyether polyol, silylated polyester,silylated polybutadiene and combinations thereof.

In some other such embodiments of the curable sealant or adhesivecomposition, either one part or two part, and its method of making, thecatalyst, may be a condensation catalyst or hardening catalyst. Examplesof catalysts or curing agents include tetrabutyl titanate andtetrapropyl titanate; organotin compounds such as dibutyltin dilaurate,dibutyltin maleate, dibutyltin diacetate, stannous octylate, stannousnaphthenate, reaction products from dibutyltin oxide and phthalateesters, and dibutyltin diacetylacetonate; organoaluminum compounds suchas aluminum trisacetylacetonate, aluminum tris(ethyl acetoacetate) anddiisopropoxyaluminum ethyl acetoacetate; reaction products from bismuthsalts and organic carboxylic acids, such as bismuth tris(2-ethylhexoate)and bismuth tris(neodecanoate); chelate compounds such as zirconiumtetraacetylacetonate and titanium tetraacetylacetonate; organoleadcompounds such as lead octylate; organovanadium compounds; aminecompounds such as butylamine, octylamine, dibutylamine,monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine,triethylenetetramine, oleylamine, cyclohexylamine, benzylamine,diethylaminopropylamine, xylylenediamine, triethylenediamine, guanidine,diphenylguanidine, 2,4,6-tris(dimethylaminomethyl)phenol, morpholine,N-methylmorpholine, 2-ethyl-4-methylimidazole and1,8-diazabicyclo(5.4.0)undecene-7 (DBU). In one embodiment, the catalystis an organotin compound such as dioctyltin dilaurate, dioctyltindicarboxylate, dioctyltin dineodecanoate, or di-(n-butyl)tinbis-ketonate.

In some other such embodiments of the curable sealant or adhesivecomposition, either one part or two part, and its method of making, thecomposition may include one or plasticizers. Examples of plasticizersinclude, phthalate ester plasticizers such as dimethyl phthalate,diethyl phthalate, dibutyl phthalate, diheptyl phthalate, dioctylphthalate, diisononyl phthalate, diisodecyl phthalate, diisoundecylphthalate, butyl benzyl phthalate, dilauryl phthalate and dicyclohexylphthalate; epoxidized plasticizers such as epoxidized soybean oil,epoxidized linseed oil and benzyl epoxystearate; polyester plasticizersderived from dibasic acids and dihydric alcohols; polyethers such aspolypropylene glycol and derivatives thereof; polystyrenes such aspoly-.alpha.-methylstyrene and polystyrene; polybutadiene,butadiene-acrylonitrile copolymers, polychloroprene, polyisoprene,polybutene, chlorinated paraffins and the like.

In some other such embodiments of the curable sealant or adhesivecomposition, either one part or two part, and its method of making, thecomposition may optionally contain additives including dehydratingagents, tactifiers, physical property modifiers, storage stabilityimproving agents, antioxidants, adhesion promoters, ultraviolet lightabsorbers, metal deactivators, antiozonants, light stabilizers, aminetype radial chain inhibitors, phosphorous-containing peroxidedecomposers, lubricants, pigments, foaming agents, flame retardants andantistatic agents.

The polyamide additive may be used to provide rheology control tosolvent-borne coatings. Examples are conventional coatings, coatingsthat are formulated as one- or two-component pack high solids coatingsystems and 100% solids coatings such as UV curable coatings and powdercoatings. In one embodiment of a coating composition containing thevarious embodiments of the polyamide described herein, the coating isbased on a binder resin chemistry selected from the group consisting ofpolyestermelamine, polyester-urea/formaldehyde, alkyd-melamine,alkyd-urea/formaldehyde, acrylic-melamine, acrylic urea/formaldehyde,epoxies, epoxy urea/formaldehyde, epoxy/amines and epoxy/amides,polyurethanes, alkyd and acrylic modified urethane, uralkyds, urethaneacrylates and urethane amide acrylates, high solids air-dry paints ofalkyd and acrylic resin, vinyl toluated alkyds, chain stopped air-dryalkyds and modified alkyds, oleoresins, polyvinyl acetates and vinylacrylics.

For the purposes of the present disclosure, the terms “high solids” and“high solids content” refer to solid contents of at least 70% by weight(wt. %), more preferably at least 80 wt. %, and most preferably at least85 wt. %, based on the total weight of the coating composition aftermixing both packs. The maximum solids content generally is not higherthan 95 wt. %. The solids content of the composition can be determinedin accordance with ASTM standard D 5201-01.

In one such embodiment, the present disclosure provides for a highsolids coating composition comprising: a first pack and a second pack;wherein the first pack comprises: (a) at least one resin (b) a polyamidecomposition having a median particle size ranging from 1 μm to 10 μm;and (c) a diluent; and the second pack comprises: at least one crosslinking agent; wherein the high solids composition has a solids contentof at least 70 wt. %, and wherein the polyamide is activated upon mixingthe ingredients of pack one between 25° C. and 50° C. Variousembodiments of a polyamide composition are described below and may beused in the foregoing high solids coating composition.

In one such embodiment of a two pack high solids paint composition, theresin is an epoxy. In one such embodiment, the epoxy resin is selectedfrom the group consisting of bisphenol A epoxy, bisphenol F epoxy, orphenolic novolac epoxy or combinations thereof. Such two component epoxysystems are cured with hardeners. In one embodiment, the hardener isselected from the group consisting of aliphatic polyamines, polyamineadducts, polyamide/amidoamines, aromatic amines, ketimines andcycloaliphatic amines and combinations thereof. In one embodiment, theepoxy system is formulated with reactive diluents to reduce theviscosity of the base resin based on bisphenol A, bisphenol F, or phenolnovolac epoxy resins to improve handling and ease of processing invarious applications. Reactive diluents typically are epoxygroup-containing functional products which are low viscosity materialsthat can react with the curing agents to become a part of thecross-linked epoxy system. Reactive diluents are described in U.S. Pat.No. 4,417,022 and U.S. Patent Appl. Publ. No. 20050192400 each of whichis incorporated by reference in their entirety.

In another embodiment of a two pack high solids paint composition withthe resin in a first pack and the resin is a polyol which forms apolyurethane when reacted with a crosslinker in a second pack. In suchembodiments, the polyol is a high molecular weight, high functionalitypolyol and the crosslinker is a low viscosity, high functionality liquidpolyisocyanate crosslinker.

In some embodiments, of the high solids paint composition, the polyolresin is independently selected from the group consisting of:polyurethane polyol, a polyester polyol, a polyether polyol, apolyacrylate polyol, and combinations thereof. For such embodiments ofhigh solids coating compositions, the amount of polyamide ranges from0.5 wt. % to 2 wt. % and the amount of cross linking agent ranges from10 wt. % to 20 wt. %.

Diluents which may be present in the coating composition includecustomary solvents, such as aromatic, aliphatic, araliphatic orcycloaliphatic hydrocarbons, partly or fully halogenated aromatic,aliphatic, araliphatic or cycloaliphatic hydrocarbons, alcohols such asmethanol, ethanol, isopropanol, butanol, benzyl alcohol, diacetonealcohol, esters such as ethyl acetate, propyl acetate, butyl acetate,ether esters such as methoxypropyl acetate or butyl glycol acetate,ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents such as dimethylformamide andwater, and mixtures thereof. VOC exempt solvents may also be used asolvents.

The coating composition may optionally contain one or more auxiliaryingredients including plasticizers, stabilizers, phase mediators,pigments, surface-active substances, defoamers, biocides, desiccants,catalysts, initiators, photosensitizers, inhibitors, light stabilizers,and preservatives.

The cross-linking agent in pack two is selected according to thecomposition of the polyol resin. In some embodiments, the cross-linkingagent is a diisocyanate or polyisocyanate. Examples of diisocyanatecompounds include p-phenylene diisocyanate, biphenyl 4,4′-diisocyanate,toluene diisocyanate, tetramethylxylene diisocyanate, 3,3′-dimethyl-4,4biphenylene diisocyanate, 1,4-tetramethylene diisocyanate,1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexane-1,6 diisocyanate,methylene bis(phenyl isocyanate), 1,5 naphthalene diisocyanate,bis(isocyanatoethyl fumarate), isophorone diisocyanate (IPDI) andmethylene-bis-(4 cyclohexylisocyanate.

In some other embodiments, the formulation may contain an aminecompound. Examples include butylamine, octylamine, dibutylamine,monoethanolamine, diethanolamine, triethanolamine, diethylenetriamine,triethylenetetramine, oleylamine, cyclohexylamine, benzylamine,diethylaminopropyline, xlylenedamine, triethylenediamine, guanidine,diphenylguanidine, 2,4,6-tris(dimethylaminomethyl)phenol, morpholine,N-methylmorpholine, 2-ethyl-4-methylimidazole, and1,8-diazabicyclo(5,4,0))undecene-7 (DBU).

In some embodiments, of the high solids paint composition, the polyamideconsists essentially of a polyamide having groups derived from: adiamine selected from the group consisting of ethylene diamine andhexamethylene diamine; a straight chain monocarboxylic acid having 1 to6 carbon atoms; a fatty acid independently selected from the groupconsisting of: 12-hydroxystearic acid, lesquerolic acid and combinationsthereof; wherein the diamine, the straight chain monocarboxylic acid andfatty acid have a molar equivalent ratio ranging from 1:1.75:0.25 to1:0.75:1.25; or 1:1.5:0.5 to 1:1:1; and a median particle size rangingfrom 1 μm to 10 μm. In some embodiments of the polyamide of the highsolids paint composition, the straight chain monocarboxylic acid isindependently selected from the group consisting of: propionic acid,butyric acid, valeric acid, hexanoic acid and combinations thereof. Incertain of the embodiments of the polyamide of the high solids paintcomposition, the straight chain monocarboxylic acid is independentlyselected from the group consisting of: acetic acid, propionic acid, andcombinations thereof.

In some embodiments of the high solids paint composition, the polyamideconsists essentially of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is acetic acid and the fatty acidis 12-hydroxystearic acid wherein ethylene diamine, acetic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In some embodiments of the high solids paint composition, the polyamideconsists essentially of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is propionic acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, propionic acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In other embodiments of the high solids paint composition, the polyamideconsists essentially of groups wherein the diamine is ethylene diamine,the straight chain monocarboxylic acid is butyric acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, butyric acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In some embodiments of the high solids paint composition, the polyamideconsists essentially of groups wherein, the diamine is ethylene diamine,the straight chain monocarboxylic acid is hexanoic acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, hexanoic acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In some other embodiments, of the high solids paint composition, thepolyamide consists of a polyamide having groups derived from: a diamineselected from the group consisting of ethylene diamine and hexamethylenediamine; a straight chain monocarboxylic acid having 1 to 6 carbonatoms; a fatty acid independently selected from the group consisting of:12-hydroxystearic acid, lesquerolic acid and combinations thereof;wherein the diamine, the straight chain monocarboxylic acid and fattyacid have a molar equivalent ratio ranging from 1:1.75:0.25 to1:0.75:1.25; or 1:1.5:0.5 to 1:1:1; and a median particle size rangingfrom 1μm _(t)o 10 μm. In some such embodiments of the polyamide, thestraight chain monocarboxylic acid is independently selected from thegroup consisting of: propionic acid, butyric acid, valeric acid,hexanoic acid and combinations thereof. In certain of the embodiments ofthe polyamide of the high solids paint composition, the straight chainmonocarboxylic acid is independently selected from the group consistingof: acetic acid, propionic acid, and combinations thereof.

In some embodiments of the high solids paint composition, the polyamideconsists of groups wherein, the diamine is ethylene diamine, thestraight chain monocarboxylic acid is acetic acid and the fatty acid is12-hydroxystearic acid wherein ethylene diamine, acetic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In some embodiments of the high solids paint composition, the polyamideconsists of groups wherein the diamine is ethylene diamine, the straightchain monocarboxylic acid is propionic acid and the fatty acid is12-hydroxystearic acid wherein ethylene diamine, propionic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In other embodiments of the polyamide, the diamine is ethylene diamine,the straight chain monocarboxylic acid is butyric acid and the fattyacid is 12-hydroxystearic acid wherein ethylene diamine, butyric acidand 12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

In some embodiments of the high solids paint composition, the polyamideconsists of groups wherein the diamine is ethylene diamine, the straightchain monocarboxylic acid is hexanoic acid and the fatty acid is12-hydroxystearic acid wherein ethylene diamine, hexanoic acid and12-hydroxystearic acid have a molar equivalent ratio ranging from1:1.75:0.25 to 1:0.75:1.25; or 1:1.5:0.5 to 1:1:1 and said polyamidehaving a median particle size ranging from 1 μm to 10 μm.

EXAMPLES

The following examples further describe and demonstrate illustrativeembodiments within the scope of the present invention. The examples aregiven solely for illustration and are not to be construed as limitationsof this invention as many variations are possible without departing fromthe spirit and scope thereof.

Example 1

To a 500 ml, 4-neck glass reactor equipped with an overhead stirrer, adean-stark trap, a condenser and thermocouple, 200.0 g (0.647 mole) of12-hydroxystearic acid (HSA) and 75.2 g (0.647 mole) of hexanoic acid(HA) was added. The mixture was heated to 75-80° C. under N₂ until allmaterial was molten. The reactor mixer was switch on and 38.9. g (0.647mole) of ethylenediamine (ED) was slowly added to the reactor within 2-3minutes. A typical exotherm increases the temperature to 135-140° C.After the temperature was held at 135° C. for 15-20 minutes, 0.13 g ofphosphoric acid catalyst was added to the reactor. The reaction mixturewas slowly heated to 180° C. and held for 5-6 hours until acid/aminenumbers are about 5-8. The material was then removed from the reactor,cooled and milled to a fine powder with a median particle size between 1and 10 microns. The amide composition is designated as HSA-ED-HA

Example 2

To a 500 ml, 4-neck glass reactor equipped with an overhead stirrer, adean-stark trap, a condenser and thermocouple, 100.0 g (0.323 mole) of12-hydroxystearic acid (HSA) and 112.8 g (0.97 mole) of hexanoic acid(HA) was added. The mixture was heated to 75-80° C. under N₂ until allmaterial was molten. The reactor mixer was switch on and 38.9. g (0.647mole) of ethylenediamine (ED) was slowly added to the reactor within 2-3minutes. A typical exotherm increases the temperature to 135-140° C.After the temperature was held at 135° C. for 15-20 minutes, 0.13 g ofphosphoric acid catalyst was added to the reactor. The reaction mixturewas slowly heated to 180° C. and held for 5-6 hours until acid/aminenumbers are about 5-8. The material was then removed from the reactor,cooled and milled to a fine powder with a median particle size between 1and 10 microns. The amide composition is designated as HSA-ED-HA (2).

Example 3

To a 500 ml, 4-neck glass reactor equipped with an overhead stirrer, adean-stark trap, a condenser and thermocouple, 200.0 g (0.647 mole) of12-hydroxystearic acid (HSA) and 47.8 g (0.647 mole) of proprionic acid(PA) was added. The mixture was heated to 75-80° C. under N₂ until allmaterial was molten. The reactor mixer was switch on and 38.9. g (0.647mole) of ethylenediamine (ED) was slowly added to the reactor within 2-3minutes. A typical exotherm increases the temperature to 135-140° C.After the temperature was held at 135° C. for 15-20 minutes, 0.13 g ofphosphoric acid catalyst was added to the reactor. The reaction mixturewas slowly heated to 180° C. and held for 5-6 hours until acid/aminenumbers are about 5-8. The material was then removed from the reactor,cooled and milled to a fine powder with a median particle size between 1and 10 microns. The amide composition is designated as HSA-ED-PA (1).

Example 4

To a 500 ml, 4-neck glass reactor equipped with an overhead stirrer, adean-stark trap, a condenser and thermocouple, 200.0 g (0.647 mole) of12-hydroxystearic acid (HSA) and 38.8 g (0.647 mole) of acetic acid (AA)was added. The mixture was heated to 75-80° C. under N₂ until allmaterial was molten. The reactor mixer was switch on and 38.9. g (0.647mole) of ethylenediamine (ED) was slowly added to the reactor within 2-3minutes. A typical exotherm increases the temperature to 135-140° C.After the temperature was held at 135° C. for 15-20 minutes, 0.13 g ofphosphoric acid catalyst was added to the reactor. The reaction mixturewas slowly heated to 180° C. and held for 5-6 hours until acid/aminenumbers are about 5-8. The material was then removed from the reactor,cooled and milled to a fine powder with a median particle size between 1and 10 microns. The amide composition is designated as HSA-ED-AA (1).

Example 5

To a 500 ml, 4-neck glass reactor equipped with an overhead stirrer, adean-stark trap, a condenser and thermocouple, 200.0 g (0.647 mole) of12-hydroxystearic acid (HSA) and 57.0 g (0.647 mole) of butyric acid(BA) was added. The mixture was heated to 75-80° C. under N₂ until allmaterial was molten. The reactor mixer was switch on and 38.9. g (0.647mole) of ethylenediamine (ED) was slowly added to the reactor within 2-3minutes. A typical exotherm increases the temperature to 135-140° C.After the temperature was held at 135° C. for 15-20 minutes, 0.13 g ofphosphoric acid catalyst was added to the reactor. The reaction mixturewas slowly heated to 180° C. and held for 5-6 hours until acid/aminenumbers are about 5-8. The material was then removed from the reactor,cooled and milled to a fine powder with a median particle size between 1and 10 microns. The amide composition is designated as HSA-ED-BA (1).

Example 6

In this example, we compare the rheological performance of polyamideadditives in a MS-polymer based sealant formulation, The rheologicaladditives were compounded without applying heat. The MS Polymer sealantformulation is shown in Table 1 and the various ingredients were mixedin a planetary vacuum mixer Type LPV 1 following a mixing procedureappropriate for sealant production. A minimal temperature rise wasobserved due to mixing. The rheology of the final materials was measuredwith a MCR 300 rheometer from Physica. The measuring geometry was aplate-plate system (PP/PE 25). For rheology assessment on the MCR 300rheometer, the MS Polymer sealant formulation was used without acatalyst.

TABLE 1 MS Polymer sealant formulation. # Component Wt parts Function 1MS-Polymer S 203 H 15.00 binder 2 Carbital 110 S 50.00 extender 3 Kronos2190 1.00 pigment 4 Rheological Additive 3.50 rheological additive 5MS-Polymer S 303 H 10.00 binder 6 Jayflex DIUP 16.50 plasticiser 7Dynasilan VTMO 0.70 water absorbent 8 Dynasilan DAMO-T 0.50 adhesionpromoter 9 Metatin 740 0.30 catalyst

TABLE 2 Rheological performance of MS polymer sealant prepared with apolyamide additive loading at 1 wt % - additive activated withoutheating. Shear Shear rate, Viscosity, thinning Yield Amide composition*s⁻¹ Pa index point HSA-ED-HA (1) 0.1 1293 81 148 HSA-ED-PA (1) 0.1 2071115 217 HSA-ED-AA (1) 0.1 687 49 nm Nm = not measurable

The data in Table 2 demonstrates that with a low activation temperature,the MS Polymer sealant formulation with HSA-ED-PA (1) polyamide providedthe highest viscosity, shear thinning index and yield point values. TheMS Polymer sealant formulations with HSA-ED-HA (1) and HSA-ED-AA (1)polyamides provided lower viscosity, shear thinning index and yieldpoint values but still imparted rheological activity.

Example 7

This example evaluates the rheological performance of MS polymer sealantmaterial with general formulation as shown in Table 1, but compounded at45° C. In addition, a 3.5 wt % polyamide additive loading was used toenhance performance differences. The results shown in Table 3 illustratedesirable performance when the amide formulation of HSA-ED-HA (1) isadjusted to the additive formulation of HSA-ED-HA (2). The HSA-ED-HA(2), and HSA-ED-PA (1) polyamide compositions show desirable rheologicalefficiency in comparison to HSA-ED-HA (1) and the industrial benchmark.

TABLE 3 Shear Viscosity at Viscosity at thinning Amide composition* Molratio 0.1 s−1 100 s−1 index HSA-ED-HA (1) 1:1:1 4938 29 170 HSA-ED-HA(2) 1:1.5:0.5 8444 32 264 HSA-ED-PA (1) 1:1:1 9464 35 270 Industrialbenchmark na 6331 32 198

Example 8

The rheological performance in a two component polyurethane paint wasexamined. Polyamides were evaluated for performance as rheologicaladditive (RA) by incorporating them in a high solids two componentpolyurethane paint system with a formulation shown in Table 4. Agenerally recommended process for the incorporation of the RA into partA of a paint was followed by adding an initial charge of resin, solventand RA to a mix tank. This mixture is then pre-dispersed at 15-20 m/sfor a specified amount of time. After this pre-dispersion step, titaniumdioxide R-900 pigment and leveling agent were added and then the mixturewas further dispersed at 15-25 m/s and at a specified batch temperatureand time so an acceptable “Fineness of Grind” is achieved. The batchtemperature was actively controlled at either 50° C. or 65° C. tosimulate paint production in a manufacturing plant.

TABLE 4 High solids two component polyurethane paint formulation. PartsComponent Supplier by Wt. Component A Acrylic Polyol in Butyl BASF(modified rapid property 31.43 Acetate development acrylic polyol, 80%solids in Butyl Acetate, Eq. Wt = 400 g/mol; OH number = 135-150)Solvent (Methyl Amyl Various 16.37 Ketone) Levelling aid BASF 0.16Rheological additive Various 1.02 (RA) TiO₂ filler Chemours (R-900 oreasily 39.33 dispersable TS-6200) Component B (Curative) Isocyanatecuring agent Bayer (aliphatic, 100% solids Eq. 11.69 Wt. = 183 g/mol;23% NCO)

The ability of the polyamide to control paint rheology was assessed bymeans of sag resistance measurement in mils using a Leneta Sag multinotch applicator at room temperature in accordance with ASTM D4400.Results for the two component A+B cured urethane paints are shown inTable 5. The HSA-ED-HA (1) polyamide does not effectively control therheology when incorporated at 50° F. in part A as the amide is notactivated into the active form at this temperature. This particularamide requires paint processing at 65° C. In contrast, the HSA-ED-PA (1)additive shows good activation at the lower 50° C. processingtemperature.

TABLE 5 Leneta SAG (mils) for 77% solids urethane coating, MAK/BAsolvent. Paint process temperature Polyamide additive 50° C. 65° C.HSA-ED-HA (1) 11 40 HSA-ED-PA (1) 44 45

Example 9

High solids polyurethane paint part A preparation was initiated atambient paint processing temperatures. The formulation shown in Table 4was followed and the RA loading level for all RA's (HSA-ED-HA (1) andHSA-ED-AA (1)) evaluated was 1.3% based on total solids of the A+B mixedpaint. An easily dispersible pigment TS-6200 was used and pigmentgrinding was done for 30 minutes at 9.4 m/s which is a relatively lowdispersion speed. This formula benefits from a type of TiO₂ which iseasily dispersible at low mix speeds. No heat was added to the paint mixpots during mixing. Batch temperatures were measured at the end of thedispersing step and it was found that this low shear rate dispersiononly raised the temperatures of the batches up to 26° C.-30° C., whichis a marginal increase above ambient temperature. Another set of paintswere prepared as per Example 8 for the two polyamide additives but thepaint processing temperatures were controlled at 65° C. The ability ofthe polyamide to control paint rheology was assessed by means of sagresistance measurement in mils using a Leneta Sag multi notch applicatorat room temperature in accordance with ASTM D4400. Results for the twocomponent A+B cured urethane paints are shown in Table 6. In contrast tothe HSA-ED-HA (1) control, the HSA-ED-AA (1) polyamide additiveactivated at ambient temperature showed excellent rheology control interms of sag resistance. The HSA-ED-HA (1) control did not activate atthis low temperature and required a 65° C. processing temperature foractivation, however, this additive was not able to match the efficiencyof the HSA-ED-AA (1) material.

TABLE 6 Leneta SAG (mils) for 77% solids urethane coating, MAK/BAsolvent. Paint process temperature Polyamide additive Ambient (26°C.-30° C.) 65° C. HSA-ED-HA (1) 13 40 HSA-ED-AA (1) 80 80

Example 10

Polyamides were evaluated for performance as rheological additive (RA)by incorporating them in a high solids two component epoxy paint systemwith a formulation shown in Table 7. A generally recommended process forincorporation of the RA into part A of a paint was followed by adding aninitial charge of resin, solvent and RA to a mix tank. This mixture isthen pre-dispersed at 15-20 m/s for a specified amount of time. Afterthis pre-dispersion step, pigment and other additives were added andthen the mixture was further dispersed at 15-25 m/s and at a specifiedbatch temperature and time so an acceptable “Fineness of Grind” isachieved. The batch temperature was actively controlled at either 50° C.or 65° C. to simulate paint production in a manufacturing plant.

TABLE 7 High solids two component epoxy paint formulation. PartsComponent Supplier by Wt. Component A Bis-A Epoxy resin MillerStephenson (EEW = 187.5 23.52 g/mol) Epoxy reactive diluent Cardolite(alkylphenol glycidyl ether; 0.65 EEW = 490 g/mol) Epoxy reactivediluent Air Products (neopentyl glycol 1.97 diglycidyl ether; EEW =137.5 g/mol) Rheological additive Various 0.90 (RA) Solvent Various 9.68TiO₂ filler Chemours 6.77 Talc filler Imerys 8.39 Sodium potassiumUnimin 6.77 aluminosilicate filler Anti-corrosion Heubach (zinccontaining filler) 1.67 pigment Calcium silicate NYCO (epoxy surfacefunctionalized 7.62 filler filler) BaSO₄ filler Cimbar 14.39 DefoamerElementis Specialties (non-silicone 0.31 aliphatic) Colorant ElementisSpecialties (black pigment 0.13 dispersion) Component B (Curative blend)Amine curing agent Cardolite (phenalkamine; AHEW = 132 11.49 g/mol)Amine curing agent BASF (C18 unsaturated fatty acid 5.74 amidoamine;AHEW = 95 g/mol)

The ability of the polyamide to control paint rheology was assessed bymeans of sag resistance measurement in mils using a Leneta Sag multinotch applicator at room temperature in accordance with ASTM D4400.Results for the two component A+B cured epoxy paints are shown in Table8.

TABLE 8 Leneta SAG (mils) for 90% solids epoxy coating, iso-butanolsolvent. Polyamide additive Paint processing temperature SAG (mils)HSA-ED-HA (1) 65° C. 37 HSA-ED-HA (1) 50° C. 23 HSA-ED-PA (1) 50° C. 73HSA-ED-AA (1) 50° C. 75

The control HSA-ED-HA (1) polyamide composition does not show effectiveactivation at lower paint preparation temperature, while the HSA-ED-PA(1) and HSA-ED-AA (1) polyamide compositions do show good activation andrheology control by means of sag resistance testing of paints preparedat lower processing temperatures.

The present disclosure may be embodied in other specific forms withoutdeparting from the spirit or essential attributes of the invention.Accordingly, reference should be made to the appended claims, ratherthan the foregoing specification, as indicating the scope of thedisclosure. Although the foregoing description is directed to thepreferred embodiments of the disclosure, it is noted that othervariations and modification will be apparent to those skilled in theart, and may be made without departing from the spirit or scope of thedisclosure.

1. (canceled)
 2. (canceled)
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 5. (canceled) 6.(canceled)
 7. A curable sealant or adhesive composition comprising: aresin; a catalyst or curing agent; optional solvent, pigment, filler,and plasticizer; and a polyamide composition consisting essentially of apolyamide having groups derived from: a diamine selected from the groupconsisting of ethylene diamine and hexamethylene diamine; a straightchain monocarboxylic acid having 1 to 5 carbon atoms; wherein thestraight chain monocarboxylic acid is independently selected from thegroup consisting of: acetic acid, propionic acid, and combinationsthereof; and a fatty acid independently selected from the groupconsisting of: 12-hydroxystearic acid, lesquerolic acid and combinationsthereof; wherein the diamine, the straight chain monocarboxylic acid andfatty acid have a molar ratio range selected from the group consistingof: ranging from 1:1.75:0.25 to 1:0.75:1.25; or ranging from 1:1.5:0.5to 1:1:1; and said polyamide composition having a median particle sizeranging from 1 μm to 10 μm, wherein the polyamide composition has anactivation temperature ranging between 25° C. and 50° C., when combinedwith the resin, and optional pigment, filler and plasticizer, andwherein the curable sealant or adhesive composition is a one part systemor a two part system.
 8. The curable sealant or adhesive compositionaccording to claim 7, wherein the resin is selected from silicone,polyurethane systems, acrylic, butyl rubber solvent based resin,epoxy-penetrating solvent-based resin, and combinations thereof.
 9. Thecurable sealant or adhesive composition according to claim 7, whereinthe resin is selected from a silyl-terminated polymer independentlyselected from the group consisting of: silylated polyurethane, silylatedpolyether polyol, silylated polyester and combinations thereof.
 10. Thecurable sealant composition according to claim 7, wherein the curablesealant composition is a one part system and is moisture curable.
 11. Amethod of making a curable sealant or adhesive composition comprisingthe steps of: adding a polyamide composition to a resin and catalystmixture; blending the mixture of the polyamide and the resin andcatalyst mixture at a temperature ranging between 25° C. and 50° C.;wherein the polyamide composition consisting essentially of a polyamidehaving groups derived from: a diamine selected from the group consistingof ethylene diamine and hexamethylene diamine; a straight chainmonocarboxylic acid having 1 to 5 carbon atoms; wherein the straightchain monocarboxylic acid is independently selected from the groupconsisting of: acetic acid, propionic acid, and combinations thereof;and a fatty acid independently selected from the group consisting of:12-hydroxystearic acid, lesquerolic acid and combinations thereof;wherein the diamine, the straight chain monocarboxylic acid and fattyacid have a molar ratio range selected from the group consisting of:ranging from 1:1.75:0.25 to 1:0.75:1.25; or ranging from 1:1.5:0.5 to1:1:1; and said polyamide composition having a median particle sizeranging from 1 μm to 10 μm.
 12. The method of making a curable sealantor adhesive according to claim 11, wherein the resin is selected fromsilicone, polyurethane systems, acrylic, butyl rubber solvent basedresin, epoxy-penetrating solvent-based resin, and combinations thereof.13. The method of making a curable sealant or adhesive according toclaim 11, wherein the resin is a silyl-terminated polymer independentlyselected from the group consisting of: silylated polyurethane, silylatedpolyether polyol, silylated polyester and combinations thereof. 14.(canceled)
 15. (canceled)
 16. (canceled)
 17. (canceled)
 18. (canceled)19. (canceled)
 20. The polyamide composition of according to claim 7,wherein the diamine is ethylene diamine, the straight chainmonocarboxylic acid is acetic acid and the fatty acid is12-hydroxystearic acid.
 21. The polyamide composition of according toclaim 7, wherein the diamine is ethylene diamine, the straight chainmonocarboxylic acid is propionic acid and the fatty acid is12-hydroxystearic acid.